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Price: high to low
Number of reviews
Price per night from
$180
NEW TO MARKET- Private Pool, WIFI, Grill, and Centrally Located to Sarasota or B
Tallevast house
3 bedrooms / 3 bathrooms / sleeps 7
Responds fast! avg. 3 hours 53 minutes
Price per night from
$168
Responds fast! avg. 43 minutes
Price per night from
$92
WIFI, Private Pool, Dock, Lido Key and Siesta Key Beaches, Close To Downtown Sar
Tallevast house
3 bedrooms / 2 bathrooms / sleeps 8
Responds fast! avg. 3 hours 53 minutes
Price per night from
$209
Responds fast! avg. 43 minutes
Price per night from
$82
Responds fast! avg. 43 minutes
Price per night from
$92
NEW TO MARKET- Private Pool, WIFI, Grill, and Centrally Located to Sarasota or B
Tallevast house
3 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 3 hours 53 minutes
Price per night from
$156
NEW TO MARKET- Private Pool, WIFI, Grill, and Centrally Located to Sarasota or B
Tallevast house
3 bedrooms / 2 bathrooms / sleeps 8
Responds fast! avg. 3 hours 53 minutes
Price per night from
$166
Great rentals within 20 miles that match your search
Responds fast! avg. 7 minutes
Price per night from
$452
Spectacular Beach House With GulfView Only Steps to a Pristine Beach
Holmes Beach house
3 bedrooms / 3 bathrooms / sleeps 6
Price per night from
$677
“Excellent” Our stay at 4638 Runabout way was amazing. We loved that the house was very nice, spacious, and clean for my family and I. We loved swimming in the pool everyday. The service was excellent all around. We would definitely stay there again.
Responds fast! avg. 2 hours 18 minutes
Price per night from
$192
“Beautiful little cottage” We stayed at this lovely little cottage on Siesta Key mid-April. The cottage is very nice, with all the amenities, even a washer/dryer for extended stays. It's cozy, with high ceilings, a nice bathroom and kitchen/living room. The bed seemed a little small (only a double), but it was very comfortable. The wireless internet was not working when we were there, which was a little frustrating. There is a beautiful pool and nice garden areas. The private beach was also very nice. All of the staff and the owner were extremely pleasant and welcoming. We enjoyed our time there.
Responds fast! avg. 3 hours 11 minutes
Price per night from
$395
2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!
Bradenton Beach cottage
3 bedrooms / 2 bathrooms / sleeps 8
“Perfect Beach House” We loved the quaint little duplex. The house was clean and ready for us when we arrived. Tim was a dream to work with. The A/C one of the units went out while we were there, and he had someone there first thing to take care of it. We will definitely be looking to rent from Tim again in the future.
Price per night from
$162
Luxury Condominium at Siesta Dunes Beachside Pool Hot Tub Tennis Sun Deck
Sarasota apartment
2 bedrooms / 2 bathrooms / sleeps 4
“Very comfortable lodgings” Loads of extras in this unit. Well cared for, updated very nicely. Disappointed that the large deck was taken out of service, possibly for a year! It seems to me that usage could have been sustained by posting signs that caution all users to wear appropriate foot-ware on the deck at all times, and to avoid running or playing on the deck. Also the deck restoration could be tackled section by section so as to retain the use by all tenants and owners.
Responds fast! avg. 3 hours 25 minutes
Price per night from
$276
Responds fast! avg. 2 hours 27 minutes
Price per night from
$350
“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!
Responds fast! avg. 1 hour 25 minutes
Price per night from
$225
Luxury Romantic Oceanfront Siesta Beach Condo #304
Siesta Key apartment
1 bedroom / 1 bathroom / sleeps 4
“What a View!” This is a very nicely decorated 1 bedroom and bath on Siesta Key Beach. You have an unobstructed view of the beach the minute you look into the condo. There's a great view from the bedroom as well! Very easy walk fo the beach..chairs and umbrella provided as well as all the amenities of home. We'd stay here again!
Responds fast! avg. 2 hours 9 minutes
Price per night from
$192
A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub
Holmes Beach house
3 bedrooms / 3 bathrooms / sleeps 6
“out standing place to stay” I would/will stay here again when we come back down. Everything is top notch and the home has everything you need. We enjoyed the pool and hot tube, used it every night. Mike and Lesley are very easy to work with and do anything to make things go smoothly.
Price per night from
$469
2 MINUTE WALK TO SIESTA BEACH!! (really) 1 MINUTE TO POOL. GREAT VALUE!!!
Siesta Key apartment
2 bedrooms / 1 bathroom / sleeps 5
“Happy Customer” We had an amazing time. The owners were so nice & made us feel so welcomed. I couldnt have been happier with our stay & we look forward to staying there again soon when life slows back down. Highly recommend this home♡
Responds fast! avg. 1 hour 34 minutes
Price per night from
$249
AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS
Bradenton Beach apartment
2 bedrooms / 2 bathrooms / sleeps 5
Price per night from
$193
Price per night from
$237
Price per night from
$210
River Strand Country Club Resort Vacation Home
Bradenton apartment
2 bedrooms / 2 bathrooms / sleeps 4
Price per night from
$150
“Beautiful inside and out. Perfect location” My family and I stayed in this beautiful rental during February 2015. We could not have asked for a more perfect spot. The rental is just steps away from the beach and has a wonderful view of the beautiful sunsets. Siesta Key Village is an easy walk away and has great restaurants and shops. We are hoping to go back as soon as we can!
Price per night from
$790
Grand accomdation on USA #1 Beach - Siesta Key Fl
Siesta Key apartment
2 bedrooms / 2 bathrooms / sleeps 5
Price per night from
$123
“Majestic Views” Our family loved our visit to Anna Maria. The house is gorgeous and spacious. My kids enjoyed the pool and eating outside. We hope to return in the near future.
Price per night from
$424
Price per night from
$282
Watch Sunsets, Dolphins, or Just Relax - Bermuda Bay 1453
Bradenton Beach apartment
3 bedrooms / 3 bathrooms / sleeps 6
“Great place, great location, and everything you need!” We stayed here to go to my sister's wedding at The Beach House. We loved this townhouse. It had spacious rooms, beautiful decor, and a great view of the ocean from the balcony. I was really impressed with how many little things were available. There were plenty of towels, soap and shampoo dispensers in the bathroom, spices in the cabinet, beach towels, and even aloe gel for burns. In the garage there is an area full of sand toys and floats and a grill. We felt so comfortable and had a true vacation.
Responds fast! avg. 3 hours 37 minutes
Price per night from
$259
Responds fast! avg. 1 hour 51 minutes
Price per night from
$202
Price per night from
$322
Luxurious 2 BR Condo - Short Walk to Siesta Beach, #1 in The USA
Siesta Key apartment
2 bedrooms / 2 bathrooms / sleeps 6
“a fine 2 weeks in Siesta” charming property, that was comfortable for four. The unit was very clean and fresh upon arrival. The neighbours were friendly and the overall property well kept. Siesta Key is a quiet community with usual shopping amenities over the causeway. This property was a brief 10 minute walk to the beach. Would we stay again, yes.
Price per night from
$154
Anna Maria Island, 2 Bed, 2 Bath Condo in quiet setting near to Beaches
Holmes Beach condo
2 bedrooms / 2 bathrooms / sleeps 4
“Great Value Stay in Paradise aMI!” This is a lovely spacious condo, nicely furnished, with decent wifi, aircon and all mod cons. The condos in the Sandy Point complex all share a pool and we found this to be very clean, nicely warm and never too crowded. Although it's on the quieter side of the island we liked the location - it's a five minute walk from Publix, even less to the free Island Trolley Bus, and less than 10 minutes to the beach for those amazing sunsets :-) The equipment cupboard allowing us to borrow beach chairs, swimming noodles, buckets and spades etc was much appreciated. Having looked around at other rentals we found this condo to be very keenly priced. Andrew and Jo were very pleasant and easy to deal with and we will definitely stay again some day.
Price per night from
$131
“Time in Paradise” We recently had the luck to spend two months in paradise. This condo was comfortably appointed, well stock to meet all our needs, and most importantly in the perfect location. The beach was a short walk to the left and stores and restaurants were just a short walk to the right. We had a great time and enjoyed everything Sarasota, Siesta Key, and this Sandy Toes Condo had to offer. Thanks Mark!
Price per night from
$268
A Siesta Tropical Retreat - Island Pool Oasis in Village & 2 blocks to Beach
Siesta Key house
3 bedrooms / 2 bathrooms / sleeps 9
“Your best choice for location!” We stayed for 10 lovely days in this home and I have to say It was an even better location than I expected. Everything you could want to do is in walking distance or you can walk to the village (maybe a 3 minute walk)and hop in a free taxi . The house is well appointed and beds are very comfortable. We traveled with a 10 yr.old, 11yr. old , and 15 yr. old my 15 yr. old niece slept in the trundle bed and commented on how comfortable the bed was. In the kitchen you will find a drawer full of menus for the many nearby restaurants and information for water activities. I highly recommend parasailing while your there ! Considering how close everything is the street is very quiet and the owners were great to deal with. Thanks Kathi and Grant!
Price per night from
$296
“Siesta Key Townhouse” This was a wonderful place to stay! The house was very clean and spacious and had everything we needed for a week at the beach.
Responds fast! avg. 27 minutes
Price per night from
$427
“Great Place for a relaxing vacation!” The place has everything you need to feel like home and relax. Perfect for family vacation. And the location is awesome - the beach two feet of the balcony.
Price per night from
$201
4 Bedroom with Gulf View Siesta Key FL Beach Fun
Siesta Key apartment
4 bedrooms / 4 bathrooms / sleeps 10
“Fantastic Location and Beautiful Accomodations” Our daughters and their families stayed here in February. The condo was everything we expected and more. It has a breathtaking view of the Gulf from the screened in lani which runs the width of the unit. The four bedrooms were perfect for our group of nine and the kitchen / dining area was well stocked with appliances , pots & pans , dishes , glassware , etc. Condo has easy access to heated pool and ample parking. Owner made the rental process smooth as silk , and we all felt right at home as soon as we had checked in. Right across street from world famous Siesta Beach. Would highly recommend.
Price per night from
$366